Hydrochloric Acid → (S)-N-(2-amino-2-(3-bromo-5-fluorophenyl)ethyl)-N-methyl-2-nitrobenzenesulfonamide hydrochloride

HRID 596016Notes

Reaction equation

HRID 596016 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:25]C(=O)OC(C)(C)C)[CH2:10][N:11]([CH3:24])[S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-:23])=[O:22])(=[O:14])=[O:13])[CH:5]=[C:6]([F:8])[CH:7]=1.[ClH:33]>C(Cl)Cl>[ClH:33].[NH2:25][C@@H:9]([C:4]1[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([Br:1])[CH:3]=1)[CH2:10][N:11]([CH3:24])[S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22])(=[O:14])=[O:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118054701tert-Butyl (S)-(1-(3-bromo-5-fluorophenyl)-2-((N-methyl-2-nitrophenyl)sulfonamido)ethyl)carbamate

Product 1

HCID 118046149(S)-N-(2-amino-2-(3-bromo-5-fluorophenyl)ethyl)-N-methyl-2-nitrobenzenesulfonamide hydrochlorideYield 67.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl (1-(3-bromo-5-fluorophenyl)-2-(N-methyl-2-nitrophenylsulfonamido)ethyl)carbamate (40 g, 75 mmol) in DCM (420 ml) at room temperature was added HCl (4M in dioxane, 150 ml, 601 mmol). The resultant solution was stirred at room temperature for 4 hours during which time a white solid precipitated out. The reaction mixture was filtered, the white solid was washed with DCM (50 ml×2), and vacuum dried to afford 23.8 grams of the desired product as a white solid. (HCl salt). (S)—N-(2-amino-2-(3-bromo-5-fluorophenyl)ethyl)-N-methyl-2-nitrobenzenesulfonamide (23.8 g, 68% yield over four steps). LC-MS: (M+1): 433.9 m/z at 0.66 min. 1H NMR (400 MHz, <dmso>) ppm 2.86 (s, 3H) 3.56-3.82 (m, 2H) 4.61 (t, J=7.24 Hz, 1H) 7.42-7.61 (m, 2H) 7.68 (d, J=1.57 Hz, 1H) 7.75-8.05 (m, 4H).

Workup

  1. customprecipitated out
  2. filtrationThe reaction mixture was filtered
  3. washthe white solid was washed with DCM (50 ml×2), and vacuum
  4. customdried

Sources & evidence

ORD record
ord-39434f72160b41808d253b75f5d130ad
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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